They started off playing soul/latin boogaloo/ reggae music in the beginning, but began focusing more on reggae music after finding out that there are many similarities between reggae and Korean traditional culture.

Windy City has played in many festivals in Korea as headliners and also played in many festivals outside of Korea including SunSet Live, Kazeno Matsuri (Japan) Fat Festival, Smiley Reggae Festival (Thailand), Young Generation of London Jazz night (UK), Mosaic festival (Singapore) and more.

They hope to find and share the original meaning of life through reggae music.